Building Addressable Libraries: Site-Selective Lewis Acid (Scandium(III)) Catalyzed Reactions

被引:22
作者
Bi, Bo [1 ]
Maurer, Karl [2 ]
Moeller, Kevin D. [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
[2] CombiMatrix Corp, Mukilteo, WA 98275 USA
基金
美国国家科学基金会;
关键词
Diels-Alder reactions; Lewis acids; microelectrode arrays; multicomponent reactions; site-selective synthesis; MICROELECTRODE ARRAYS; TRIFLUOROMETHANESULFONATE;
D O I
10.1002/anie.200902350
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reagent confinement: Lewis acid catalyzed reactions have been conducted on arrays with either 1024 or 12 544 microelectrodes cm-2. A Sc III species generated at the electrodes is employed as the Lewis acid, and the reagent is confined to the electrodes through the use of a solutionphase reductant. A multicomponent synthesis of a tetrahydropyran (see scheme), a Diels-Alder reaction, and an esterification reaction are all compatible with this strategy. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5872 / 5874
页数:3
相关论文
共 17 条
[1]   Antigen detection using microelectrode array microchips [J].
Dill, K ;
Montgomery, DD ;
Wang, W ;
Tsai, JC .
ANALYTICA CHIMICA ACTA, 2001, 444 (01) :69-78
[2]  
Hintsche R, 2000, ELECTROANAL, V12, P660, DOI 10.1002/1521-4109(200005)12:9<660::AID-ELAN660>3.0.CO
[3]  
2-#
[4]   Building Addressable Libraries: Site-Selective Suzuki Reactions on Microelectrode Arrays [J].
Hu, Libo ;
Maurer, Karl ;
Moeller, Kevin D. .
ORGANIC LETTERS, 2009, 11 (06) :1273-1276
[5]   Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides [J].
Ishihara, K ;
Kubota, M ;
Kurihara, H ;
Yamamoto, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4560-4567
[6]  
Itoh T, 2004, HETEROCYCLES, V63, P2769
[7]   Straightforward access to a structurally diverse set of oxacyclic scaffolds through a four-component reaction [J].
Jiménez, O ;
de la Rosa, G ;
Lavilla, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6521-6525
[8]  
Jimenez O., 2005, ANGEW CHEM, V117, P6679
[9]   Microelectrode arrays and ceric ammonium nitrate: A simple strategy for developing new site-selective synthetic methods [J].
Kesselring, David ;
Maurer, Karl ;
Moeller, Kevin D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11290-+
[10]   Building addressable libraries: Site-selective formation of an N-acyliminium ion intermediate [J].
Kesselring, David ;
Maurer, Karl ;
Moeller, Kevin D. .
ORGANIC LETTERS, 2008, 10 (12) :2501-2504